JP2016130806A

JP2016130806A - 静電荷像現像用トナー

静電荷像現像用トナー Download PDF

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Publication number: JP2016130806A
Authority: JP; Japan
Prior art keywords: group; toner; resin; carbon atoms; substituted
Prior art date: 2015-01-14
Legal status : Pending

Application number

JP2015005416A

Other languages

English (en)

Japanese (ja)

Other versions

JP2016130806A5 (cg-RX-API-DMAC7.html

Inventor

萱森　隆成

Takanari Kayamori

隆成萱森

健太郎茂木

Kentaro Mogi

健太郎茂木

規之金原

Noriyuki Kanehara

規之金原

Current Assignee

Konica Minolta Inc

Original Assignee

Konica Minolta Inc

Priority date

2015-01-14

Filing date

2015-01-14

Publication date

2016-07-21

2015-01-14 Application filed by Konica Minolta Inc filed Critical Konica Minolta Inc

2015-01-14 Priority to JP2015005416A priority Critical patent/JP2016130806A/ja

2016-07-21 Publication of JP2016130806A publication Critical patent/JP2016130806A/ja

2017-07-13 Publication of JP2016130806A5 publication Critical patent/JP2016130806A5/ja

Status Pending legal-status Critical Current

Links

238000011161 development Methods 0.000 title abstract description 5
229920005989 resin Polymers 0.000 claims abstract description 167
239000011347 resin Substances 0.000 claims abstract description 167
229920001225 polyester resin Polymers 0.000 claims abstract description 110
239000004645 polyester resin Substances 0.000 claims abstract description 110
229910052751 metal Inorganic materials 0.000 claims abstract description 105
239000002184 metal Substances 0.000 claims abstract description 105
150000001875 compounds Chemical class 0.000 claims abstract description 98
239000003086 colorant Substances 0.000 claims abstract description 96
239000011230 binding agent Substances 0.000 claims abstract description 23
239000006185 dispersion Substances 0.000 claims description 136
125000004432 carbon atom Chemical group C* 0.000 claims description 76
125000001424 substituent group Chemical group 0.000 claims description 57
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 37
239000002253 acid Substances 0.000 claims description 31
125000006165 cyclic alkyl group Chemical group 0.000 claims description 25
125000005843 halogen group Chemical group 0.000 claims description 17
238000002156 mixing Methods 0.000 claims description 17
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 13
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229920000728 polyester Polymers 0.000 claims description 12
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 11
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 10
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150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
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230000007774 longterm Effects 0.000 abstract 1
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239000010419 fine particle Substances 0.000 description 144
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238000000034 method Methods 0.000 description 56
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239000012736 aqueous medium Substances 0.000 description 25
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238000005259 measurement Methods 0.000 description 18
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238000007792 addition Methods 0.000 description 13
238000004220 aggregation Methods 0.000 description 13
125000002947 alkylene group Chemical group 0.000 description 13
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239000010410 layer Substances 0.000 description 11
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239000011777 magnesium Substances 0.000 description 10
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238000011282 treatment Methods 0.000 description 10
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229910052802 copper Inorganic materials 0.000 description 9
229910052749 magnesium Inorganic materials 0.000 description 9
229940091250 magnesium supplement Drugs 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
235000019333 sodium laurylsulphate Nutrition 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
230000004931 aggregating effect Effects 0.000 description 8
239000011258 core-shell material Substances 0.000 description 8
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
229910052791 calcium Inorganic materials 0.000 description 7
239000011575 calcium Substances 0.000 description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
230000008859 change Effects 0.000 description 7
238000001035 drying Methods 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
229910052742 iron Inorganic materials 0.000 description 7
239000000463 material Substances 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
239000003505 polymerization initiator Substances 0.000 description 7
238000007639 printing Methods 0.000 description 7
229920002554 vinyl polymer Polymers 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
125000004423 acyloxy group Chemical group 0.000 description 6
125000003368 amide group Chemical group 0.000 description 6
125000004104 aryloxy group Chemical group 0.000 description 6
239000011248 coating agent Substances 0.000 description 6
238000000576 coating method Methods 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
239000011572 manganese Substances 0.000 description 6
150000002736 metal compounds Chemical class 0.000 description 6
238000012360 testing method Methods 0.000 description 6
229910052725 zinc Inorganic materials 0.000 description 6
239000011701 zinc Substances 0.000 description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
125000003277 amino group Chemical group 0.000 description 5
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125000003118 aryl group Chemical group 0.000 description 5
238000004140 cleaning Methods 0.000 description 5
238000000113 differential scanning calorimetry Methods 0.000 description 5
238000004945 emulsification Methods 0.000 description 5
230000009477 glass transition Effects 0.000 description 5
150000008040 ionic compounds Chemical class 0.000 description 5
125000005647 linker group Chemical group 0.000 description 5
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229940051841 polyoxyethylene ether Drugs 0.000 description 5
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239000011164 primary particle Substances 0.000 description 5
HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 5
238000012546 transfer Methods 0.000 description 5
PGMMMHFNKZSYEP-UHFFFAOYSA-N 1,20-Eicosanediol Chemical compound OCCCCCCCCCCCCCCCCCCCCO PGMMMHFNKZSYEP-UHFFFAOYSA-N 0.000 description 4
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
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230000032683 aging Effects 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
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230000000903 blocking effect Effects 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
239000012986 chain transfer agent Substances 0.000 description 4
229910017052 cobalt Inorganic materials 0.000 description 4
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GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
JJOJFIHJIRWASH-UHFFFAOYSA-N icosanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCCCC(O)=O JJOJFIHJIRWASH-UHFFFAOYSA-N 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
239000000314 lubricant Substances 0.000 description 4
229910001629 magnesium chloride Inorganic materials 0.000 description 4
229960002337 magnesium chloride Drugs 0.000 description 4
239000000693 micelle Substances 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 4
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000002356 single layer Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000006228 supernatant Substances 0.000 description 4
239000010936 titanium Substances 0.000 description 4
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
HCEPYODGJFPWOI-UHFFFAOYSA-N tridecane-1,13-diol Chemical compound OCCCCCCCCCCCCCO HCEPYODGJFPWOI-UHFFFAOYSA-N 0.000 description 4
XSMIOONHPKRREI-UHFFFAOYSA-N undecane-1,11-diol Chemical compound OCCCCCCCCCCCO XSMIOONHPKRREI-UHFFFAOYSA-N 0.000 description 4
LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 4
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
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XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
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230000007423 decrease Effects 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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238000010907 mechanical stirring Methods 0.000 description 3
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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239000012188 paraffin wax Substances 0.000 description 3
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